help with things to do in Tuscany/Umbria

Old Oct 15th, 2010, 12:17 PM
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sue878, I second your recommendation for a visit to Sant' Antimo. A lovely spot to picnic before or after listening the monks' chants. I loved the calmness of the place, and the whimsical carvings of animals in the stonework. There is a tiny underground altar near the front of the Abbey, with sweet, faded frescoes of cherubs. Here is a link:
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Old Oct 15th, 2010, 01:44 PM
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annabell2, I loved the calmness of the place also. Thanks for the link, I forgot to add it.
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Old Oct 15th, 2010, 04:52 PM
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How about rafting on the River Corno? Rafting Umbria,, has 2 hour rafting expeditions on a 7km stretch of the river. The trip starts 6km west of Norcia which is south of Perugia and east of Speleto. The tour includes equipment and guides and runs through gentle stretches as well as some exciting white-water rapids.
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Old Oct 15th, 2010, 06:34 PM
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Raspberries to those above who would suggest that time in rural Tuscany equals nothing to do! My family and I had a 3 part trip to Italy -Venice - Aegean Sea cruise - Montepulciano, and the latter was the high point of our trip. Here is an except from my notes - of note, the town of Monticchiello has a restaurant called La Porta that people raive about - could not get in - and nearby is an estate worth visiting called La Foce:

The winery tour is very highly recommended, both for the delightful tour they give you as well as for the quality of the Vino Nobile wine. (
Montepulciano is situated between the Valleys of the Chiana and the Orcia rivers. Most people feel the Val d’Orcia is the more picturesque of the two, but - wow – both are just incredibly beautiful.
Had a lovely 3 hour tour of two local wineries. Scenery is simply indescribable. Wine was equally fantastic. Following that we checked into the little Albergo (hotel) la Terrazza ( run by the charming, if not slightly eccentric, Roberto. Roberto runs a fine hotel, part time enoteca, and claimed to be the ex-goalkeeper of the town football club as well as the current President of their local league. While there, I engaged in a nice conversation with a Canadian guest who is of Italian ancestry who knew the area well and she suggested a day trip itinerary for us for the next day. We visited the famous Temple of San Biaggio (16th century), the Abbey of Sant Antimo (11th) the Castiglione (fortress) d’Orcia (12th) – went swimming in a hot spring fed pond in the town of Bagno Vignoni, had lunch in the tiny hilltop hamlet of Monticciello, and ended at a small farm ( Cugusi - that made, on the premises, their very own sheep’s milk cheese called pecorino and a very high quality Olive Oil. – An outstanding itinerary and easy to do. – In particular the drive from Bagno Vignoli to Monticchiello is not on many maps, very rural, and just left me slack-jawed with the beauty of the landscapes.

I am confident you will leave Montepulciano and Perugia wishing you had more time there.
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Old Oct 16th, 2010, 09:25 AM
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And here is my Tuscany offering. I did this itinerary for a friend:

Take the Chiusi/Chiancino exit off the A1 & take the N146 to Montepulciano. Leave Montepulciano toward Pienza. Your hotel, La Saracina, is about half way between Montepulciano & Pienza. The hotel has a small sign on the left (south) side of the road just after another sign that says you are leaving Montepulciano. The hotel is to the left & about 100 yds up a cypress-lined dirt road.

Hotel La Saracina, just east of Pienza. This is one of our 2 favorite “hotels” in Europe - just 5 rooms in this old restored farmhouse with fabulous views. The property has vineyards, olive trees, swimming pool, tennis court, & a very nice breakfast room. Each room has a separate living room /bedroom, with a huge bath area . The bathroom has a shower, spa, & huge sinks . We had the “Malvasia” room which was the best. On another visit we stayed at the “Trebiano” room next to Malvaisa, which was also fabulous.
Phone 0578 748 022 fax 0578 748 018

La Saracina is out in the countryside. If you want to stay in a town, and experience Italian village life and walk to restaurants, a good choice would be the Palazzo del Capitano in San Quirico. The 2 suites are fantastic and there is a very lovely & large garden with chaise lounges for relaxing after a day of touring the countryside, taking hikes, and visiting the hilltop villages. There is a nice restaurant at this hotel, but we have never dined there (it was closed in March when we visited.)
e-mail [email protected]

Dinner La Grotta, next to the big church you see below Montepulciano on the west side of the city. If you drive toward Montepulciano from Pienza, you can’t miss the church – it is quite a site. (picture taking)

Day 13
Tuscany – Val d’Orcia
My wife & I first visited the Val d’Orcia (around Pienza) in the late ‘80s when we were doing the typical “once over lightly” tour of Italy. On an old map I used at the time, I had scribbled the comment “pretty” on the road running between San Quirico d’Orcia and Montepulciano. We passed though this area again on several subsequent visits – usually staying 1 or 2 days each time. In September ’94, we stayed 4 days at the 5-room Hotel La Saracina near Pienza, and explored the area a little more (using up a lot of film) and then moved on to the Chianti area for 3 days, San Gimignano for 2, Lucca for 2, etc. In September ’96 we met 3 other couples (old college friends celebrating our 25th anniversaries together) for a 4 day stay in La Saracina. One of the couples liked the area so much that they booked a 3 week stay at La Saracina the next year, and then bought a 2nd home in the town of San Quirico the year after that (after exploring Chianti & Umbria to make sure they were buying in the area they liked the most). In ’99 when we retired early so we could travel more, we stayed in their apartment for 3 weeks - taking day trips to other areas in Tuscany & Umbria, exploring the Val d’Orcia, and enjoying Italian village life in San Quirico. That same year we had spent a considerable amount of time in Provence (7 weeks), and when we arrived in the Val d’Orcia, we both commented that this area was the prettiest countryside we had seen anywhere in Europe. I have various books & posters showing the Val d’Orcia in early spring when everything is green. It looks quite different in these spring pictures than it does in September when we had always been there. In March of ‘04 when the airfares were low and our friends were living in their apartment in San Quirico for 5 months, we visited the Val d’Orcia again. We thought that in September the countryside looked remarkable with the fields freshly plowed, exposing the soil with colors ranging from dark rust to light tan, with the cypress trees dancing up hills or running along the crest of a ridge, farmhouses tucked here & there, medieval villages everywhere, castles, vineyards, olive groves, and virtually no ugly commerce to spoil the scene (like elsewhere in Tuscany). Well, March is even prettier. The winter wheat that is planted almost everywhere is bright green and when it catches the late day sun, it is really spectacular with all the rolling hills, cypresses, farmhouses, etc. Our friends in San Quirico say it’s even more scenic in late May or early June when it’s still green, but the wheat is taller and blows in the wind. Since our 3 week stay in ’99, we have visited Vermont during leaf season, Provence several more times (including poppy, lavender & sunflower seasons), the Dordogne, Alsace, Pays Basque, Scotland, Bavaria, the Cotswolds, and many places in between – but we both feel that the Val d’Orcia is the prettiest open countryside we have seen anywhere. When we were there in March, we took several day trips to other sections of Tuscany, and when we returned “home” we always commented “why do we travel anywhere else in Italy – there’s nothing prettier than where we are staying”. So, for the remainder of our 2 week trip, we didn’t travel anywhere else – we spent all our time finding more nooks & crannies in the Val d’Orcia.

The following is a 1 day driving itinerary through this area, with stops at various villages and sites. If you have more time to spend in this vicinity, by all means drive down some of the dirt roads and even take some walks.

The best times of day to see this area are in the early morning or late afternoon when the sun is lower in the sky. When the shadows are long, the cypress trees & umbrella pines look more pronounced as they “dance up the hill” (my wife’s term). The farmhouses sprinkled throughout the landscape take on a special look in the early morning and at sunset. Budget at least two rolls of film for this area. The Val d’Orcia can get some morning fog. If so, spend the morning in a village & start your drive when the fog lifts.

In my opinion, the countryside is the “star” in this part of Tuscany. You “must see” Pienza and there are other interesting villages too, but don’t shortchange the drive through the countryside. If you are behind schedule, skip some villages – not the countryside. You might think that this itinerary seems out of order in places & I’m often taking you down roads that you have already driven. Sometimes, I’m considering the position of the sun when you drive on a road, and other times I’m just trying to extend the time to enjoy the countryside.

You will need the Touring Club Italiano map of Tuscany to follow this route. Also, obtain the Michelin Green Guide to Tuscany. If anyone wants to take walks in this area, get the Carta Turistica e Stradale – Val di Chiana, Val d’Orcia map. They have it at the bookstore in Pienza.

If you are doing this tour as a day trip from Siena, leave Siena going south on the N2 (marked SS2 also). It’s actually a pretty drive. Just past the second turnoff to Montalcino and past the bridge, look for a beautiful grove of cypress trees to your right. At San Quirico, take the N146 east to Montepulciano. This is an easy drive. If you leave Siena by 7:00 you should get to Montepulcano by 8:30 or earlier.

Do not visit Montepulciano at this time, unless it is foggy in which case you should wait until the fog lifts before proceeding on this drive. Take the N146 west to Pienza. The sun will be at your back. When you pass the large domed church of San Biagio (on your right/north) just after leaving Montepulciano, look back towards Montepulciano & you will be rewarded with a spectacular site – the Church of San Biagio in the foreground with Montepulciano cascading down the hillside behind it. This is one of the most photographed sites in Tuscany. Before I retired, I had a giant poster of this view in my office – reminding me why I wanted to retire & spend more time traveling. Don’t take a picture just yet – you will be back over this route later in the day and the sun will be in a better position to shine on the church and the perched village behind it.

Continue on the N146 to Pienza. This road has some wonderful scenery. You should get to Pienza by 9:00.

As you approach the “old” part of Pienza and the N146 turns right towards San Quirico, make a sharp left turn and you will find some parking spaces. If these parking spots are filled, continue down this road & look for the blue parking (P) to your left. During tourist season, you have to pay to park in this lot. You can also park south of Pienza below the village, but you will have a slight climb uphill to the center of town.

Explore Pienza by entering through the Porta al Murello, at the west end of Pienza. Just as you enter Pienza, there is a nice pottery/gift shop on your left (in the large square) which has had a significant impact on my wallet. Most stores open at 9:30 & close for a 1 ½ to 3 hr lunch at 1:00 (typical in Italy). You can obtain a self guided 1 hour audio tour of the town (in English) by renting a head set from the tourist office (closed at lunch time, but open on Sunday). If you want to have a picnic lunch at Sant’ Antimo abbey, pick up some lunch provisions while in Pienza. There is a pizza shop just outside of the Porta al Murello (next to the book store/news stand) where you can pick up a slice of pizza. There is a walking path next to the town walls on the south side of Pienza – don’t miss this. It’s a great place to just sit in the sun & admire the views. Plan on spending 1 ½ hrs in Pienza if you take the audio tour or you’re a big shopper, 1 hr if not. It’s one of the few villages in Tuscany that has most of it’s stores open on Sunday, & Monday mornings.

Leave Pienza on the N146 toward San Quirico. This is another stretch of road with fantastic views – perhaps our favorite. Just 2K from San Quirico, there is a splendid view to the south of a very small church and another building with cypress trees & umbrella pines surrounding these buildings. This site is on the crest of a hill. If you have been in Tuscany for any length of time, you will have seen this view on many postcards & calendars. You will pass this church again later in this drive when the late afternoon sun makes this scene perfect for picture taking. As you approach San Quirico, drive into the parking lot behind the Taverna del Barbarossa restaurant (which is associated with the Casanova hotel). The parking lot is at the south end of the complex. Park the car, get out & you will see another of the most photographed sites in Tuscany. In fact, the very first picture that appears in my ’95 Michelin Green Guide to Tuscany, is a photograph of this scene – a farmhouse sitting on top of a hill, surrounded by cypress trees. A “coffee table” book I have has photographs of this site at different times of the year – it’s quite remarkable. This site is even on the cover of that book. I also have a poster (yes, it was hanging in my office too).

You should get to San Quirico by 11:00 if you stopped for some picture taking along the way. Don’t visit San Quirico now – do so later in the itinerary if you have time (it’s worth a visit).

Follow the signs at San Quirico and get on the N2 toward Siena (north). Just after you leave San Quirico on the N2, you will be on a bridge. If you look back, there is a nice view of the village of San Quirico from the bridge. Unfortunately, I have never been brave enough to get out of the car & take a picture from this bridge. Further along the N2 there is a pretty grove of cypress trees on your left (west). This grove can be seen better traveling south, however. On your right, you will see several cypress trees and umbrella pines dotting the ridge of a hill. You might recognize this site from postcards & calendars you have seen. Turn off the N2 & go to Montalcino.

As you approach Montalcino, you will get some good views of this perched village. The road will turn a few times & will take you to the south entrance of town, which will be marked with a large “Montalcino” painted on a white background on the stone wall of town, and a “centro” sign will be pointing into town . Do not enter through this entrance - instead turn a very sharp left when you see this town sign and follow the road uphill. Very shortly you will see a round-about. Exit to the right off the round-about to find a place to park. There is a rather large car parking lot near the old fortress (Rocca). Note – When you arrive into Montalcino and encounter the round-about, note the sign to Sant’ Antimo Abbey (marked “S. Antimo”), where you will go next on this itinerary (it’s marked on the round-about). The road to this abbey is a very sharp left (almost a full circle around the round-about).

Visit Montalcino. You should get there by 11:00. Many shops will close by 1:00. You can visit the fortress, but I found it only OK. Budget about 1 hour or less in Montalcino. It has some nice outdoor lunch spots if you want a sit down lunch (I’m pushing the picnic at Sant’ Antimo).

Follow the signs (and your map) to Sant’ Antimo Abbey. The Abbey is quite lovely, but what I like best about it, is the setting – we’ve used up a lot of film there. It’s located in a valley surrounded by hills, cypress trees dancing up these hills, and a lawn around of the Abbey (where you can picnic). It’s also a good place for a little snooze in the sun. There are Gregorian chants inside the church at various times of the day (posted on the entrance to the church – one chant is at 12:45). See for a full chant schedule and a description of Sant Antimo.

Continue on your drive through the countryside. You should leave Sant’ Antimo about 1:30. Take the road south-east of the abbey, toward Monte Amiata on your Touring Club map. Pass through Monte Amiata, and at Ost. Ansidonia, turn left (north-east) to Castiglione d’ Orcia. This is pretty countryside. Pass through Castiglion & get on the N2 & head north toward San Quirico. You should get to San Quirico about 2:00 or so.

Continue past San Quirico toward Siena. You will have another chance to see the cypress grove to your left, and the cypresses & umbrella pines running along the ridge to your right. Get off the N2 at Torrenieri. There is a road that runs from Torrenieri to San Quirico, just east of the N2. Find it on the Touring Club map. You want to head south on this road from Torrenieri to the “phantom” village of Bellaria on the map (there really isn’t any village there). When driving through Torrenieri just after leaving the N2, you need to turn right at the first stop sign (in front of a small church) and you will immediately cross a railroad track. As you approach Bellari, look to your right and you will see more umbrella pines & cypress trees dotting the top of a ridge. These are the same trees you saw from the N2 on your drive to Montalcino and to Torrenieri. When you get to Bellaria, turn left (east) to Cosona (it’s marked at the turn). You will be on a dirt road. It is one of our favorite drives in this area. Continue & go slowly on this dirt road. Lots of pretty sites here. This dirt road will kind of dead-end onto another road (see it on your map). Turn right toward Pienza and continue on toward Pienza. When you get to the N146, turn west (right) toward San Quirico. You should get here around 3:00.

About half way to San Quirico, there is a dirt road that heads south of N146 – find it on the map (it’s the only one on the map between Pienza & San Quirico). There is a sign for this road on the N146 and the turn is marked by a direction sign to the “Agriturismo il Rigo”, and before a “watch for deer” sign. Turn south on this road. We have often driven down this road, parked the car, & started on a hike from here. Continue on this road until it connects with the N2.

Continue south on the N2, and after about 2K, head east on the paved road (marked yellow on the touring club map) toward Chianciano & Pienza (well marked). This road passes through another “phantom” town called Spedaletto – find it on the map to make sure you turned at the right place off the N2. This road goes trough the heart of the Val d’Orcia and is quite picturesque. Continue on this road toward Chianciano Terme. You will have a nice view of Pienza perched on top of a ridge, off in the distance to the left (north). There is an “interchange” on this road – pay attention & keep heading to Chianciano Terme. Just before La Foce, you will see a lovely double set of cypress trees to the north, dancing (again) up the hill (another much photographed site). Continue on this road, and shortly you will see a parking lot opposite the Restaurant Oasi la Foce. Pull into this lot & you will get another view of this double set of cypress trees. Continue toward Chianciano, and about 1/2K after the parking lot, take the first left (north) on a dirt road toward Montepulciano (well marked). This will be a dirt road and will pass around a lovely castle. When the dirt road becomes a paved road, turn left towards Monticchiello (well marked). As you approach Monticciello, this road becomes particularly scenic.

Monticchiello is a very cute village – it’s where my father-in-law says he wants to live. Park the car in the lot outside this village near the refreshment stand (do you need any) & wander around. It’s a 30 min wander. There is a nice restaurant in town called La Porta.

Look at Monticchiello on the Touring Club map. You will see lots of roads radiating from this small village like spokes on a bicycle wheel. All these roads have fantastic views of the countryside – in my opinion, they offer the prettiest drives in the Val d’Orcia. If you have time to spare, by all means drive down all these roads. We’ve done this quite often at various times of the day when the sun casts different shadow patterns on the rolling hills and from the cypress trees. My favorite drive is the one branching out at 8:00 from Monticchiello. It connects to the road heading directly north to Pienza. Turn right towards Pienza on this road & you will get a fantastic view of Pienza. Just a little south of Pienza, there is a dirt road that heads south-west. Take this road and it will connect with the N2/Chianciano road running east/west. From here you can retrace the drive east towards La Foce where you will head to Montepulciano (by-passing the turn to Monticchiello). When this road hits the N146, turn left to Montepulciano.

If you don’t have extra time available for this side trip, after visiting Monticchiello head back down hill from the parking lot. Immediately after leaving the lot, go straight at the fork (just after the first house on the right) instead of turning right the way you entered the lot. This will lead to Montepulciano on a paved road that shortly becomes a dirt road and later paved again. There is a nice view of Montepulciano from this road. When this road dead-ends at the N146, turn left towards Pienza, or right to Montepulciano if you want to visit this town (one of my favorites).

Visit Montpulciano, if you like (1 hr visit). Use the Michelin Green Guide to find the sites you want to visit. Hike all the way up to the Piazza Grande. It’s a somewhat steep walk through town, however, but the village is very pretty. You can taste some excellent wine at the Avignonesi estate (you will see it – just opposite the tall column in the middle of the main street, just after you enter town). If you need a snack, find a place where you can get pizza by the slice & have a mushroom (fungi) and truffle (tartufi) pizza (only in Italy!!!).

Leave Montepulciano towards Pienza on the N146 again. Now you get a better view with the remarkable San Biagio Church in the foreground and Montepulciano in the background (you may have to drive a little west on the N146 to get the view). Hopefully you are at this spot about 5:00 or so. Without any further stops, you are less than 1 ½ hrs from Siena.

Drive along the N146 toward Pienza & San Quirico again (30 min drive). The sun will be in your face, but now the little church with the cypress trees around it will look quite different, as will other sites you photographed when you drove this route in the morning.

If time allows, visit San Quirico (it’s 45 mins to Siena from SQ). San Quirico is kind of a poor man’s Pienza – but they like it that way. It’s a town where people really live. In fact, I’ve told friends that San Quirico is the type of town we wish our small towns in the US would be like – kind of a River City, Iowa (Music Man). Everyone knows everyone else, people are out strolling, there are stores where locals shop for their everyday stuff, etc. Families congregate at the Bar Centrale (closed Thurs) in the evening, where the men play cards in one room, the younger children are in the video room, and the older children are outside playing soccer in the town square or just hanging out. If you visit San Quirico, have a coffee latte at the Bar Centrale & “people watch”. SQ is a 30-45 min visit. Some stores may be closed Wednesday afternoon.

Further reading suggestions:
War in the Val d’Orcia by Iris Origo
This is a woman’s diary of happenings in this area during WWII. “Non-political, it is an elegantly simple chronicle of daily life at La Foce, a manor in Tuscan no-man’s land bracketed by foreign invasion and civil war. The Marchesa Origo’s faithful record is one of those rare and precious accounts that give the truth of history with the art of a gifted writer, that bear witness nobly to ignoble times.” The preceding was lifted from the back cover of the book. While we were there in ’02, they were celebrating the 100th anniversary of her birth.

Dinner Latte de Luna in Pienza. Check to make sure it is open.

Note on restaurants in this area. Except for La Grotta, Re di Macchia, Osteria del Vecchio Castello, & Pogio Antico, we found that most of the restaurant menus were pretty much the same. Nothing outstanding, but typical Tuscan fare. Don’t expect to find any gourmet treats in this area (except for the above 4). Probably the best thing to do if the weather is nice is to opt for simple outside dining. The following is a list of restaurants we have tried that have outside tables:
Al Vecchio Forno in San Quirico
Osteria il Tinaio in San Quirico
Latte de Luna in Pienza
13 Gobbi in Montefollonica
Locanda La Costa in Montefollonico (we did not dine here, but it looked nice)
All of these restaurants are in the Michelin except Al Forno & Latte de Luna

Day 14
Yesterday’s route took you through some of the most scenic countryside in the Val d’Orcia. If you want to drive around on your own and explore a little further out, here is a rough geographical description of the area that I think is the most scenic between Siena and Lake Bolsena to the south:
Find Monte San Savino on the map. Draw a line from there to about ½ inch west of Sinalunga, to about ½ inch east of Montepulciano, to ½ inch east of Chianciano, and then down the A1 to Orvieto. Everything west of this line I have found to be very scenic, and everything east is not so scenic, in my opinion. If you explore the area from Orvieto, to Todi, to Spoleto, and to Trevi, you will find the villages & scenery enjoyable too. Assisi is one of my “must see” towns and so is Perugia, but the area around these cities is not that great (especially around Perugia). As I mentioned earlier, the countryside around Cortona & Arezzo is not scenic (didn’t take the road from Arezzo to Sansepolcro, which is described in my books as nice). As you go from Bibbiena, to Poppi, to Dicomana, the drive is quite pretty. The Strada dei Sette Ponti (Road of 7 bridges) from Pontassieve (just east of Florence) to Vallombrosa, to Reggello, to Castelfranco to Loro (pretty village) is also quite beautiful.

Visit Montepulciano** in the AM. This is a good town to explore. Pick up a slice of pizza for lunch from one of the many vendors

Drive through the area north of the N146 in the afternoon & see some of the small perched villages:
Petroio, Trequanda, Montisi, Castelmuzio. This area is very scenic.

Visit Monte Olvieto Maggiore Abbey, This is a working Benedectine Abbey. The setting is pretty.
Open 9:15 – 12:00 & 3:15- 5:45.

Visit Murio & the Etruscan museum (west of Monte Olvieto Maggiore Abbey on the other side of the N2). You have probably driven past many advertisements for this town & museum – the ads look like a cartoon character with a cowboy hat (locals joke it’s a caricature of George Bush). The “character” is actually an Etruscan statue in this museum. The town of Murio is interesting to visit and the road that leads southeast through Bibbiano is very scenic.

Radicofani*– south of San Quirico off the N2 to the east. This is a large medieval fortress perched on a hilltop. You can see it from miles around. The view from the top of the tower is fantastic. The drive down the N2 is pretty too.

Dinner Osteria del Vecchio Castello*. This is a Michelin 1 star, and the restaurant is lovely. It’s in an old stone house next to a church. In March ’04 we had a very nice fixed price 6 course dinner, which was 124E for 2 including a bottle of wine. The restaurant is hard to find, but it is a very lovely drive to get there. It is in the town of la Pieve (actually, the restaurant/church complex is the town) which is south-west of Montalcino. Leaving Montalcino, first follow the signs to Tavernelle, then your map to la Pieve. Allow 45 mins to get there from Pienza. The return is easier – follow the signs to Montalcino. Take some cash with you – when we dined there, their credit card machine was not working (our friends say this happens quite often – usually at the fancier restaurants - hummmm)

Day 15
Head south from San Quirico on the N2 (marked SS2). This is a pretty drive & you will visit some appealing medieval towns in a hidden corner of Tuscany. Just after the southern most Radicofani exit (see the map) & before the small Pte d. Rigo (marked on the Touring Club Italiano map) head southwest on a small road – it goes through Sforzesca. I think there are signs directing you to Pitigliano & Sorano. Follow this road through S. Valentino to Sorano*. The next three towns you will be visiting are in the Green Michelin guide to Tuscany under “Pitigliano”. The approach to Sorano is very pretty – get the camera ready. Explore Sorano on foot. Not much happening in town, but it’s fun to wander around – several artisan shops. Leave Sorano to the south, drive to Pitigliano*, and get the camera ready again. This is our favorite town of the three. Historic Pitigliano has been beautifully & tastefully maintained. Several lunch spots available in town. Next drive to Sovana* & explore this town (not quite as interesting as the other two). Leave Sovana going west and then take the first road going southwest. This road hits another east/west road that goes back to Pitigliano. I am taking you on this route so you can see the view of Pitigliano from the south. Get the camera ready again as you approach Pitigliano. After the view, head east to Acquapendente. Get there by going through Onano – the N2 south of Acquapendente has some really ugly commerce on it. Take the N2 back to San Quirico/Pienza.

Dinner Pogio Antico* (recently lost it’s Michelin star) This was one of the best meals we had in Italy on our ’96 & ’99 trips. They have a fabulous 5 course fixed price dinner for about $50. The restaurant is a little hard to find. Allow an hour to get there from your hotel (this will allow you some time to get lost – if you don’t get lost the drive is 30 mins or so). Make sure you leave to find the restaurant in the daylight. As you drive into Montalcino, look for the sign to Poggio Antico on your left – probably on the round-about. You will drive quite a ways out of town, and then down a long dirt road to your right off the paved road.

Day 16
Spend more time in the Val d’Orcia. You should stay at least 4 days in this area (we’ve spent over 2 months there & we’re still discovering new places).

Drive to San Quirico from Pienza (if you are staying in Pienza), and when you approach San Quirico, go over a bridge, and the arched town gate is directly in front of you. Immediately turn left in front of the gate (don’t go through the gate - expensive ticket if they catch you). Continue down this road at the east end of San Quirico and park there for a visit (lots of public parking available – free). There is a stairway up to town at the south end (far end) of this car park. There is even something happening on Sundays in San Quirico (many stores close Wednesday afternoon). Have a café latte at the Bar Centrale .

Return to your car & continue in the same direction you were driving (south). The road will turn to the right around SQ, and there is a stop sign at the south entrance to town (where you entered on foot). Continue straight and head to the small town of Ripa d’Orcia (southwest of San Quirico). This road is quite scenic. Ripa d’Orcia is actually a castle with a rustic B&B (It’s in the Karen Brown guide – our friends stayed there when they were buying their home in SQ). You can’t go into the castle unless you are staying there or having dinner there (rustic dinner too). Turn around & drive to Vignoni. They were restoring the largest building in this town when we were there in March ’04 and it will be apartments. Continue on this road to Bagno Vignoni. This is a bath/spa town with old Roman bath ruins that are quite interesting. There is a spa/hotel in town. You can purchase a day pass for the spa even if you don’t stay at the hotel (our friends have done this many times). I’m not a spa person, but the spa complex looks like a resort hotel you might find in Mexico or Hawaii. The “pool” is fed by a heated water source. It has walkways over the pool as it winds around, and there are lots of lounge chairs where people catch some “rays”. We were there on a Sunday on a cold but sunny day in March and there was lots of activity. The actual town was quite nice too with many/all stores open on Sunday. There are lots of restaurants/ delicatessens with outdoor dining tables for picnics. There is another 90 room “super spa” being built nearby just outside the center of town that is scheduled to open April 1 ‘04, but when we were there on March 28 it looked like it was months away from opening. Our friends said that this hotel first started the planning process in ’80. People in Tuscany like to keep things beautiful and planning is a lot of give & take. The hotel looked very pretty & blended in with the countryside quite well. Great views from the hotel.

Dinner your choice

Day 17
Siena*** This is our favorite larger town in Italy.

It is only an hour drive from Pienza, so you can certainly visit it as a day trip from Pienza, but I think it is much better to stay overnight in Siena so that you can fully enjoy one of the most charming cities in Europe. There is nothing quite like wandering through the Campo in the late evening.

If you decide to do it as a day trip from Pienza, there is a trick to parking. Head north on the Via Cassia (N2/SS2). This is actually a scenic drive most of the way. This will take you directly into Siena (don’t take the interchange to the left as you get near Siena – many cars will be taking this left). Follow the signs to Porta Romana, which is the old town gate. As soon as you see an arch over the road, park the car. This will be a metered area (with parallel street parking).

If you are staying overnight, the hotel is close to another Porta. This is the Porta Laterina. You can actually drive through this porta, drop off your bags, let the car sit for a short while, & then park it outside this gate. Ask the hotel how to park the car. I did this without difficulty. It will be best to get to Siena early in the morning before it gets crowded.

Remember, Siena will mostly close down for a 3 hour lunch, and some stores will be closed on Monday morning (always the ones my wife wants to shop in).

The Campo*** is one of the most beautiful squares in Europe.

Visit the Duomo*** This is perhaps our favorite medium sized church in Europe. Get there early in the morning before 9:00am. Once we were the only ones there at this time once, & there were 100s of people there by noon. When visiting, look for some devices where you can insert some Euros & the device will light up the pulpit, mosiac floor, or whatever – it’s worth it.

Next to the Duomo is the “Museo dell opera Metropolitano”. We have never visited the museum, but the view from the tower on top is the best in Siena. Climb to the top – it is not difficult. You can see all the terra cotta rooftops & the maze of streets below – even the Campo.

On the other hand, the tower on the Campo is a difficult climb. It is cramped & if you get a little claustrophobic, don’t do it. My wife & I both climbed it & if you don’t mind the narrow & low twisting stairs, the view from the top is fantastic.

Wander around Siena. Read the guide books to find the interesting streets & sights. Duck into any courtyards you can find – they are usually interesting. Have lunch on the Campo (on the shady side). The shops are great: ceramice, Florentine paper, tassels, linens, leather goods, & simply “pretty” storefronts to enjoy.

Hotel Palazzo Ravizza. This is centrally located with big rooms, a delightful garden, & moderately priced.
Dinner There is nothing like dinner on the Campo. It’s touristy, but watching the sun set on the campo & the belltower is unforgettable. Just pick any place that looks appealing.

Day 18
Visit Siena in the AM if you haven’t gotten your fill.

Volterra** Notice how the landscape changes as you drive to this town. Have lunch here. Nice Church. This is a town specializing in alabaster items; lots of shops with beautiful alabaster.

San Gimignano*** This is one of the most unique towns in Italy. It is also one of the most popular tourist attractions. We have visited it 5 times & we always return. The trick is to arrive into town after 4PM when the “day trippers” start to leave, and then stay overnight in the town. It is quite peaceful in the late evening & early morning.

There is a trick getting to the hotel. You must enter following a specific route, drop off your bags, & then park the car in one of the guarded lots. Ask the hotel how to get to the guarded lot. You may even need a sticker from the hotel to allow you into town (I don’t remember). When you book the hotel, ask them if you need one and have them mail it to you along with a map of how to access their hotel.

Hotel - La Cisterna. We have always stayed here & have found it to be one of the best bargains in Italy. Nothing fancy, but it is perfectly located & they speak English.

Dinner –The hotel has a very nice dining room. Insist that you get the room with the beamed ceiling. This place hosts a lot of tours, so often the entire dining room is completly booked. If you can’t get the room with the beamed ceiling, don’t settle for the “other” room – it is not as nice. Eat at Dorando. It is not a quaint place, but actually has much better food. We have dined at Dorando twice.

Wander around town after dinner. There are good shops which are open late and even during lunch.

Day 19

The area between Siena & Florence is the Chianti region of Tuscany. A little more mountainous & rugged than southern Tuscany, but just as charming.

In the Green Michelin Guide for Tuscany, in the CHIANTI section, there are 3 driving itineraries outlined. I suggest that you follow these.

Visit the Brolio* estate. You can’t go inside the house, but the grounds are nice.

Visit Volpia

Hotel & Dinner – Villa la Barone in Panzano. This may be a good time in your trip to relax. The hotel is very peaceful – you may not want to leave. The price of the room includes dinner. Enjoy the views, take some hikes, read by the pool.

Day 20
Continue touring the Chianti area

Day 21
If you want to see some sites, you can drive to some of the Medici villas around Florence & visit them. Poggio a Caiano** is nice.

Stu Dudley
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Old Oct 16th, 2010, 01:19 PM
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Did you go on the whitewater raft trip? How was the scenery and do you know the rating? thanks
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Old Oct 17th, 2010, 09:26 AM
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Stu has shared some great ideas - certainly does counter the assertion that time in Southern Tuscany can be boring! Thanks Stu for that recap, I have not traveled as extensively, but when I was driving on the road from Spedaletto to Montichiello, I was in such awe of the incredible beauty there I pretty much threw out my bucket list of other places in the world I wanted to experience. So it's nice to know I shouldn't waste my time trying to find locations that can top the scenery we experienced in the Val d'Orcia, since no such place exists . And yes, late May is a great time to visit. Folks will undoubtedly accuse Stu of hyperbole; NOT!! I assure you this place is awesome!!

A few additions: If you can handle the climb, a climb to the top of the Tower just to the East of Castiglione d'Orcia will reward you with the most commanding view of the entire valley.

Bagno Vignoni is qutie lovely - be careful as the parking is meterred and the meter maids are aggressive! - However, just as you are turning off the main higway to approach Bagno V., there is a small dirt road to the left that will lead to a small pool where lots of locals frolic in the mineral water for free.

I am surprized Stu praised the town of Pienza so vigorously, yet did not mention the joys of shopping for Picorino, the local sheep's milk cheese this area specializes in. If you like cheese at all, you owe it to your self to check out any one of several "formaggia" in the area. One example is the Formaggi Cugusi Silvana (no web stie - suggest you google all three words.)

In Montepulciano, the city hall doubles as a nice museum, right in the Piazza Grande Centrale. If you proceed on the Via del Teatro, which comes off the main Piazza to the Southeast, you find a very fine gellateria; one more block to the east of this, take a left on the long North South running street called via del Opia nel Corso (or just "the Corso" with plenty of shops and restaurants. Again, if you want to stay in Montepulciano, the Hotel La Terrazza, will not be the most luxurious choice, but may be the most fun, as it is a delightfully eccentric facility.
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Old Oct 17th, 2010, 10:29 AM
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Bookmarking for our 3rd one-week stay in Montepulciano, one week from now.....
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